Ben Stiller: Facing His Past

Summary

Podcast Summary: All There Is with Anderson Cooper

Episode: Ben Stiller: Facing His Past
Date: December 10, 2025
Host: Anderson Cooper
Guest: Ben Stiller

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Episode Overview

In this emotionally raw episode, Anderson Cooper sits down with actor, writer, and director Ben Stiller to explore the many layers of grief, memory, and family legacy. The conversation is set against the backdrop of Stiller’s documentary film, "Stiller and Nothing is Lost," which chronicles his journey sorting through his late parents’ belongings. Anderson and Ben share their parallel experiences of loss, the struggle to face their pasts, the cyclical nature of grief, perfectionism inherited from their parents, and the ongoing challenge of breaking familial patterns.
The episode is honest, confessional, frequently humorous, and threaded with insight relevant to anyone navigating grief or family history.

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Key Discussion Points & Insights

1. The Timelessness and Evolution of Grief

(00:33–02:18)

• Anderson begins by playing a listener voicemail from Grace, who lost her mother to suicide five years prior. Grace expresses frustration with people insisting that a particular year is always "the hardest" and worries about when—if ever—grief gets easier.
  • Quote – Grace (00:33):
    "Every year at least one person has told me that the year I'm in is the hardest year … What year is the easiest? When will I have the easiest year? And I really hope I haven't already had it."
• Anderson reflects on how others’ attempts to categorize or timeline grief can feel invalidating, sharing Nick Cave’s wisdom:
  • Quote – Nick Cave (02:41):
    "There was some years, or a year at least, of absolute, devastating, incapacitating sorrow … You think that it’s simply unbearable, and you learn ultimately that actually it’s not. You can bear it."

2. Confronting the Past Through Belongings

(03:35–07:36)

• Ben Stiller describes starting to go through his parents’ things almost immediately after his father’s passing in 2020, driven by a sense of panic as the apartment felt like "home base."
  • Quote – Ben Stiller (04:13):
    "It was kind of like this knee-jerk react of, like, I just, I'm not gonna remember this place fully. I wanna just film it so I can."
• Stiller discovered an unexpected treasure trove of cassette recordings, including family moments and old sketch improvisations—each item or artifact triggering deep memories or new revelations.
• Anderson empathizes, having amassed untouched boxes in his own basement, and both relate to the overwhelming, sometimes Sisyphean, nature of sorting through a lifetime of belongings.

3. Memories, Artifacts, and Emotional Weight

(06:01–09:31)

• Stiller reflects on artifacts like old glasses and suitcases, imbuing intensely personal meaning to mundane objects.
  • Quote – Ben Stiller (06:17):
    "They're part of your parents … There's something just very heavy about that, too."
• Both men reminisce about growing up amidst New York’s quirky 1970s scene, peppered with household parties, famous guests, and family rituals.

4. Making Sense of Upbringing and Patterns

(09:31–12:51)

• Anderson ponders the effort to make sense of growing up in a storied family, saturated with sensory impressions and cultural icons.
• The discussion turns to the risk of unconsciously repeating their parents’ patterns—especially the prioritization of work over family—and the challenge of self-awareness.
  • Quote – Ben Stiller (12:03):
    "What happened is like my relationship with my work became very important to me and probably like out of balance with really attending to all the relationships in my life."

5. Perfectionism, Legacy, and Generational Repetition

(12:51–17:48)

• Perfectionism emerges as a defining trait on both sides; both Anderson and Ben describe its isolating, sometimes joyless, consequences.
• In a raw audio excerpt from Stiller’s parents, his mother laments her husband’s inability to enjoy their successes because of his relentless striving.
  • Quote – Ann Meara (17:48):
    "It is joyless. Absolutely joyless."

6. Active Grieving and Emotional Openness

(19:18–24:33)

• Anderson and Ben discuss whether they have truly grieved their parents, recognizing a shared tendency to keep up "deflector shields."
• Stiller shares a spiritual moment of feeling his mother's presence while at her old boarding school, underscoring how subtle triggers can evoke meaningful connections with the departed.

7. Learning How to Grieve

(23:52–25:51)

• Anderson admits he spent his life suppressing grief, until pursuing conversations with others helped him learn about grieving as an active, multidimensional process.
  • Quote – Anderson Cooper (23:29):
    "I need to actually grieve. I need to actually feel, allow myself to feel … and it’s been life changing."
• He cites lessons from Stephen Colbert and Francis Weller: grief as a gift, and the idea that one's relationship with the dead can continue to evolve.

8. Newfound Empathy, Acceptance, and Connection

(24:33–26:06)

• Stiller describes how sorting through family history increased his appreciation of his parents and built unexpected bonds with others experiencing similar loss.
  • Quote – Ben Stiller (25:51):
    "The understanding a little bit more what it is to be a person, and … I feel better. I feel a little better about all of it, you know, like, because it’s out in the open."

9. Societal Constraints on Grief Conversations

(26:06–28:34)

• Both men lament how open dialogue about loss or death remains taboo on television and in society.
• Anderson points out how even fleeting public acknowledgments of grief (like his annual New Year’s Eve comments) evoke enormous gratitude from viewers who feel seen.

10. Regrets and Mortality

(28:34–31:15)

• Stiller shares discomfort at hearing old tapes where his parents express sadness over his emotional distance; now, as a parent of adult children, he sympathizes with both sides.
• Stiller discusses his prostate cancer diagnosis and how confronting mortality brought bouts of gratitude and new perspective on the fragility of life.

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Notable Quotes & Memorable Moments

• Grace (Listener, 00:33): "What year is the easiest? When will I have the easiest year?"
• Nick Cave (02:41): "You think that it’s simply unbearable, and you learn ultimately that actually it’s not. You can bear it. And all sorts of extraordinary things happen within this thing that we call grief."
• Ben Stiller (04:13): "[After my dad died] it was kind of like this knee-jerk react of, like, I just, I'm not gonna remember this place fully. I wanna just film it so I can."
• Ben Stiller (06:17): "They're part of your parents. I don't know. There's something just very heavy about that, too."
• Anderson Cooper (09:31): "I'm trying to make sense of what happened. Like, what was this entire experience of growing up in the family that I grew up in ... saturated with colors and the smell of Rigo candles and cigarettes and clinking glasses and people drinking."
• Ben Stiller (12:03): "What happened is like my relationship with my work became very important to me and probably like out of balance with really attending to all the relationships in my life."
• Ann Meara (Ben's mother, 17:48): "It is joyless. Absolutely joyless."
• Anderson Cooper (23:29): "I need to actually grieve. I need to actually feel, allow myself to feel … and it’s been life changing."
• Ben Stiller (24:33): "The people who are really close to you and that have made an impact and are a part of you ... those relationships go on and continue."
• Ben Stiller (25:51): "I feel better. I feel a little better about all of it, you know, like, because it’s out in the open."
• Ben Stiller (30:02): "When you get a diagnosis like that, everything stops ... all of it’s like, wait a minute, this is something that could change everything."

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Timestamps for Important Segments

• 00:33: Listener "Grace" shares her experience of long-term grief and the recurring expectation of when it will “get easier.”
• 02:41: Nick Cave’s philosophy on the endurance of grief.
• 04:13: Ben Stiller describes the urgent instinct to document his parents’ apartment and possessions right after losing his father.
• 06:17: The power of physical objects as memory triggers.
• 12:03: Admitting to repeating parents’ work-centric patterns, unintentionally sidelining relationships.
• 14:14–15:22: Ben’s conversation with his own son, directly confronting the effects of his absence.
• 17:48: Ann Meara's candid assessment of her husband’s perfectionism ("It is joyless. Absolutely joyless.").
• 23:29: Anderson’s realization about the need to actively grieve after discovering his late father’s essay.
• 24:33: Ongoing relationships with loved ones after loss.
• 30:02: Facing mortality: Ben Stiller on learning he had prostate cancer.

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Conclusion & Takeaways

This intimate, searching conversation deconstructs the myths and expectations around grief, revealing its long, unpredictable, and deeply personal journey. Anderson Cooper and Ben Stiller find kinship in their struggles—and discover, through both humor and heartbreak, that active remembrance, candid conversation, and the courage to face emotional pain are the foundations for healing.
Their stories affirm: Grief is not a problem to solve, but a relationship to nurture—one that can, with time and honesty, grow richer and more generous.

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For further engagement:

• Ben Stiller's film "Stiller and Mira: Nothing is Lost" is streaming on Apple TV.
• To share your own story or connect with others, visit the "All There Is" community at cnn.com/allthereis.

Transcript

[A]

Welcome to all there is. I've been listening to voicemails and videos we've received over the last few weeks. They're deeply moving and I'll be putting together a special episode of the podcast soon, which is made up of them. You can record a video and email it to us if you want. The address is allthereisnand.com. you can also message the videos to us on Instagram at allthereis and you can leave us voicemails at 404-827-1805. We'd love to hear from you. I want to play you a message I heard just this morning.

[B]

My name is Grace. One thing I've learned in my grief now being almost five years since my mom died by suicide, I've learned, especially as we're approaching the holidays, that the best place to be on a holiday for me is where there's no expectations of me and where I don't put expectations on myself because I think I have to make a good impression or I think I'm bringing the mood down. And it took me a while, four and a half years. I didn't find it, but I did. She's my high school chemistry teacher and I've been babysitting her kids and I go to birthday parties and I go to Thanksgivings and Christmases and if I want to talk about my mom, they listen. And if I want to cancel at the last minute, I won't hurt anyone's feelings by choosing you and your grief on holidays. You may ruffle feathers like I do with my blood family. That's for me on holidays. I feel like those are the days where I let myself just pick me. One thing I'm going to ask though. Someone told me yesterday that they read a book that said the fifth year of Grace is hardest and I responded by telling them every year. At least one person has told me that the year I'm in is the hardest year. The first year is the hardest, the second year is the hardest, the third year is the hardest. And I asked them what year is the easiest? When will I have the easiest year? And I really hope I haven't already had it because living without my mom for five years is just too many and I just one day I'll surpass her in age and I also surpass the time that I had with her and I don't want to think about that and I don't know what to do. Yeah, so if anyone's left a voicemail telling you what year is the easiest, I'd love to know.

[A]

It can be hard when you hear others put a timetable on grief or opine on how you should feel or what you should do. I'd never say it gets easy, but it can and does change. It can and does get easier. I think about what Nick Cave said on last week's podcast about the transformation he Underwent after his 15 year old son Arthur died.

[C]

There was some years, or a year at least, of absolute, devastating, incapacitating sorrow at the time. You think that it's simply unbearable and you learn ultimately that actually it's not. You can bear it. And all sorts of extraordinary things happen within this thing that we call grief. That way of thinking is something that comes through time. It's not some sort of failure if you're not feeling that way. It takes a long time. It takes a long, long time. But.

Beautiful things often do. You could say.

[A]

We'll be right back with actor, director, writer Ben Stiller, who spent the last few years going through the things his parents left behind.

Welcome back. My guest today is actor, writer and director Ben Stiller. His mom, Ann Meara, died in 2015 and his dad, Jerry Stiller, in 2020. They were a famous comedy duo. And Ben has spent the last several years going through and making a film about all the things they left behind. It's called Stiller and Nothing is Lost and it's playing now on Apple tv.

Thank you so much for doing this.

[C]

Yeah, it's great to be. Really appreciate it.

[A]

You and I have something in common, which is we both went through our parents stuff. Did you wait a while to start going through stuff?

[C]

No. When my dad died. He died in 2020, in May of 2020. And like a week or two after that, I started going through stuff. I kind of got this like weird sort of like panic. It was the apartment I grew up in. It was the place we always went back to. And it just. It's home. It felt like home base. So then to think about it not being in our family and that was because they were leaving the apartment to my sister and I knew she wanted to sell it. It was kind of like this knee jerk react of like, I just, I'm not gonna remember this place fully. I wanna just film it so I can.

[A]

You wanna document it?

[C]

Yeah, that was the instinct. I really am like a very visual person. So like just to have those visuals of the place, you know, to be able to look at it and study it and kind of like just remember it or if I was ever thinking of it, that was the main Impetus. But then there was also. Then, of course, all this stuff of theirs.

[A]

Did you know that your dad had made cassette recordings of conversations? Do you know you had this library.

[C]

I didn't know we had all of these. Hundreds of hours of that were a combination of cassette recordings. Everything from my dad having, like, a little mini cassette recorder to record my kids, you know, as a grandparent, to going back to these reel to reel tapes that he would record their improvisation sessions that they would do to write their sketches.

[A]

I did this by myself going through these boxes, and I found it. That's the reason I started this podcast, because I found it to be such a kind of lonely and.

Fraught process. It's so heavy of opening up these boxes, even talking about it.

[C]

When you start thinking about it, it's just there's so much stuff there that every single piece, whether it's a photograph or a cufflink or.

You know, these little tchotchkes and things that just ended up in the drawer by my mom's bedside table, every single one of them would kind of take you down, could take you down a whole avenue of.

[A]

Memory, or everything is infused with memory.

[C]

Yeah. That sort of feeling. A piece of them or a connection. I'm like, trying on some glasses, and they're actually. They're my mother's father's glasses. And that suitcase that we have is my mom's father's suitcase that she had saved that I'd never looked at before. But the glasses I find very personal because that's something that someone wore every day.

[A]

And their eyes looked through that. Into your eyes.

[C]

Yeah. And then it becomes these artifacts. They're like. They're part of your parents. I don't know. There's something just very heavy about that, too.

[A]

My basement is still full of these boxes, and I just have not.

[C]

It's really.

[A]

I just can't do it.

[C]

It's kind of a crazy. Yeah, it's kind of like a crazy Sisyphean type of thing. Yes.

[A]

Yeah.

[C]

Because you're like, always. I, like, go through stuff and then it's like, okay, I'm gonna put this stuff over here and this stuff over here. But then it's also like, then what? What am I gonna do with that? And then like, how do you dig into that stuff, too? How do you start that process? Because when you start to listen to a tape, that's like an hour of my parents improvising and talking, I mean.

[A]

There must be thousands of hours of recording.

[C]

I know there's hundreds that we found and that really takes you down the rabbit hole. It's something fascinating to me about hearing just the sounds of the apartment and the phone ringing in the background or things like that that make it feel so real and in the moment.

[A]

Well, also seeing Those old Super 8 films that your dad shot, I mean, it's so New York, circa 1972. 73. I had the same jacket you wore. Like, there was snow on the streets and snow days and just funky sneakers.

[C]

And snow days were exciting.

[A]

Hair, big hair, and just messiness. And, you know, we watched Wonderama.

[C]

Yeah, we watched. I went to Wonderama once.

[A]

Every kid who would go to Wonderama would get, like, a glazed bagel with their name on it on a necklace.

[C]

Right?

[A]

And they would always wear it to school, and they'd be like, oh, yeah, no, Yeah, I was at Wonderama.

[C]

Yeah.

[A]

To go to Underra. I was like. But it's interesting because part of the thing for me in going through these boxes, which is really difficult, and I'll take a box and I'll think, okay, I'm gonna make progress today. I'm gonna do a box. And it's a box of Christmas cards from 1974. Like, how meaningful can this be? And I'm going through it, and then some of it are people who I knew. And I remember Walter Mattham. His wife Carol, was my mom's best friend. Una Chaplin and Charlie Chaplin's Christmas cards. See, that's incredible.

Because everything feels like a piece of my mom or my dad or my past. And yet it's not right.

[C]

Yeah, it's hard. Like, you start to organize stuff, and then you're like, well, what is this, then? What do I do with this? Ultimately, I think it's. I hear my dad's voice in my head when I'm doing it, because he was very much about saving stuff. It's funny, though, because it gets exhausting, too, in the moment, when you're doing it. I think after a little while, it just gets tiring, too, because you have to stop everywhere. Yeah. And then you're like. Well, and then you start to get, like, a little bit, like, I guess, like, do I keep the Charlie Chaplin Christmas card or not? You know, I don't know. No, let's put it in. In other words, you, like, get a little wiped out in the moment, and you kind of forget even, like, how. Like, how much this. It's like you just keep all this stuff. It's great to have it. And then you do find, I think, the little things that mean something to You.

[A]

I've come to the realization I'm trying to make sense of what happened. Like, what was this entire experience of growing up in the family that I grew up in that's so, in my mind, like, saturated with colors and the smell of Rigo candles and cigarettes and clinking glasses and people drinking.

[C]

And it's so funny to have so.

[A]

Many similar and, like, parties at the house.

[C]

Parties at the house.

[A]

Famous people who you see on television suddenly in your house. My parents gave. When Charlie Chaplin came back to America after being in exile to receive a special Academy Award, he and Oona flew to New York first, and my parents gave him a big welcome party. And there's a photo in the New York Times of me shaking Charlie chaplin's hand in 19. I was six or seven years old.

[D]

Wow.

[C]

Did you know?

[A]

Yeah. They gave me a whole course of study of. We watched Charlie Chaplin films, but, of course, he looked nothing like the Little Tramp. So I was like, who's this old guy? But for you, was it a sad thing to do this?

[C]

I think ultimately, even if you feel a little closer or you learn something, you are left feeling the sadness of, I still miss them. And all of this searching and all of this connecting or making a movie or writing about it or anything. Ultimately, at the end of the day, you're still dealing with just reality of what it is to be a human being and not have people around who you loved. For me, making the movie, the first two and a half years of working on it were not, like, very happy. There were so many times when I didn't want to deal with. Really deal with going into that stuff. Yeah. Because when. Cause when you do go into it, it brings up the different feelings. I think both of our childhoods, we were around adults a lot who were partying and living their lives in that way that parents in the 70s did, which was, for us as kids, it's like we had to figure it out on our own.

[A]

Yeah. My mom took me to Studio 54 when I was 11 twice.

[C]

So, you know, I went to Studio 54 when I was 13.

[A]

No.

[C]

This is so weird. It was like letting children into Studio 54, basically.

[A]

I'm obsessed with the patterns of history that run through families and how we find ourselves repeating the patterns of those who come before us. You grew up with these parents who were working constantly, who needed to work to support the family. They were on the road a lot.

[C]

Yeah.

[A]

And then you had kids and you ended up repeating the pattern of your parents with your kids.

[C]

I did yeah. And I think about how that happened because always being aware of thinking, oh, I don't want to make mistakes that my parents made or things they did as parents that weren't, you know, the best. But I think for me, what happened is like my relationship with my work became very important to me and probably like out of balance with really attending to all the relationships in my life.

[A]

I well understand the perspective you have about your work. It is the same I have and it is very difficult for anybody around me. I get laser focused and I'm a perfectionist. Like, it's so obvious the way it has to be and nothing else is acceptable and no one else understands this. I'm just trying to make it perfect. That's all I want.

[C]

Yeah. These are the people in your life who love you. Yes.

[A]

These are the people in your life.

[C]

Exactly. And then once the work goes away and when you're old and on your deathbed, these are the people you hope are around.

[A]

Yeah. And they're not going to be around. I want to be present in the lives of my kids. And yet I watched this and I realize it's not enough to think that and to realize that.

You actually have to work on it every single day and take action on it, which I.

[C]

Think is an advantage when you do have kids, when you're not super young, because.

[A]

What are you saying?

Yeah, I'm 58. Okay, fine. I know I started lake and.

[C]

No, you got it together. No, but I wasn't super young myself. I was 35 or 30. Right. That's not really young to have kids. But even then I think if I had him now, it would be a whole different thing because I think I do have a little more self awareness in that area. Or maybe it's cause I learned it through trial and error. But there was a blind spot for me. As much as I had these ideas about my parents and what they got right and what they didn't get right, it didn't jibe with my ambitions or my creative drive. I didn't understand that I was actually doing the same thing. You know, that's the thing that I'm kind of like, wow, that's really like. I really missed that.

[A]

There's a conversation you have in the film with your son. Let's play that.

[C]

Okay. You know, after a tough day, you know, or something was going wrong, you can get very much in your own head, you know what I mean? And I think once you kind of go into that place, hard to get you out of it. So that Would kind of put a damper on the, you know, fun part about being on vacation. You know what I mean? You have all these hats that you're trying to balance, you know, being a director, an actor, you know, a producer, a writer, but also just like a father. Right. And sometimes I felt that that would come, you know, last to these other.

The irony is I thought I was doing so much better than my parents. I thought I was pulling it off. I was flying home on the weekends and having special places for the kids to play when they come visit the set. But in reality, and just hearing them talk about it, for them, it was the same thing I was going through as a kid. And I just couldn't see that at all at the time.

[A]

I find that devastating.

[C]

Yeah. Even when I listen to it, I'm like, I was not expecting him to say last. When he said, you know, I thought he was gonna say, like, maybe like, not at the top of when he said last. It was like.

But like, look, it's valid because that's his experience. We all learn as you have kids and they get older, that kids take in everything we took in as kids, they're taking in.

[A]

That scene made me think, my 5 year old, what is he gonna say in 20 years? I am actively thinking, okay, what do I need to do now? I mean, I've already made. I feel like I've made.

[C]

But the fact that you're asking those questions honestly is that's all you can do. You know what I mean?

[A]

Well, you can do more than that. You can actually.

[C]

Right. Of course you can actually change it. Well, let's not go too far. But even to be aware of it is the key, you know, and all you can do is do the best you can.

[A]

But that perfectionism is something your dad had as well.

[C]

100%. Yeah. Almost all the time. I feel like he was in his head, which, again, I really identify with.

[A]

There's a conversation that he recorded between your mom and him. It's essentially an argument where your mom is saying, and we'll play it in a second, that he's just joyless. That he's so perfectionist that he sucks the joy out of everything.

[D]

I know the work and what. How people respond to you and how great your performances are. Under these conditions, no matter what, you are always there. I know all this. I'm aware of it. And then at the end, when things go halfway decently.

Your relief is embarrassing. It's like you're just, oh, God. God, it was so great. It was so you know, how do you go over how you're thought of as a good guy? I do want to be thought of as a good guy. Yes, I know. It doesn't clutter my mind. And no. And, you know, we're looked upon very lovingly by people. Nobody's wrong. Now, look at that. One thing. What? Before either of us leave this planet, there has to be some way you can get an authentic sense of your telling without worrying how you're perceived. It is joyless. Absolutely joyless.

[A]

And I have been accused of this as well. And I agree.

[C]

Me, too. And also, I agree, too. Like, that's what hit me when I heard her say that was also like, yeah, that is. I've had that feeling sometimes when I stress out about something so much, like doing something on the Oscars or something, where it's like a pressure moment to be funny or deliver, which is. I don't love doing those kinds of things because of that. Because what happens is I stress out so much about it that, you know, and then if it goes well, it's literally what she says. I'm just relieved, you know, it's not like I'm happy, like, oh, it's great. It's like, no, I'm relieved. I think my mom was also responding to, like, her relationship with my dad in terms of how he was with people, because he was incredibly outgoing and generous and genuine in his interest in other people and connecting with people and wanting people, as he says, to like him. Which I, again, like a very human thing that I really identify with, too. But my dad, he didn't have any issues to say, yeah, I want everybody to love me. Cause I didn't really get loved when I was a kid, you know.

[A]

We'll have more with Ben Stiller in a moment. If you want to listen or watch past episodes of this podcast, you can do that wherever you get your podcasts or. Or at our grief community [e-mail] allthereis you can also watch our new weekly companion show there. All There is live Thursday nights at 9:15pm Eastern. We'll be right back with more from Ben Stiller.

Do you feel like you grieved your parents?

[C]

I still feel like I'm going through that.

I have these moments of.

You know, I think making the movie for me was a way to address connecting with my grief.

Because I have such a barrier towards really opening up to that, I think. And maybe similar to you in that way, where if you made a documentary about your mom, your process in making this podcast, like you can take what you do and use it as a way to help yourself work through stuff. And I actually think that that's a lot of what art is and creativity is. It shouldn't be indulgent self therapy or whatever that nobody wants to see. And by the way, that was a concern I had, too, in making the movie. But I do think that being able to do this and have a way to delve into it through quote, unquote, work or, you know, creative process was a way in for me to, like, start to connect with them. And now what I think it's opened up is I have these moments by myself where I try to connect with my parents a little bit.

[A]

Do you feel them?

[C]

I have.

[A]

Do you feel anything?

[C]

No, that's. That's the issue.

[A]

No, but I mean, I'm joking, but. But look, I'm saying. I'm asking. I'm saying this. Somebody.

[C]

Sometimes I do, but I know it.

[A]

When I see it. But to go through life not feeling anything.

[C]

Well, if you're like me, it's like somebody's going through life. You have to kind of like, put up the deflector shields, right?

[A]

Yes.

[C]

No, I. Yeah, but the problem is you get used to having them up and then when you let them down. But, yes, I've had these weird moments, little spiritual kind of connection moments that I like. They sound so silly, but, like, of a moment when you meet somebody or something and you feel like you're somehow connecting with your parent. Have you ever had that?

[A]

Yeah.

[C]

I was at West Point scouting for a movie. You know, West Point up the Hudson. And I knew my mom had gone to boarding school up there at a place called Lady Cliff Academy that was in Highland Falls, New York, And I had never been able to find it. And I was in the West Point Visitor center. And I asked somebody, I said, hey, there's a place called Lady Cliff Academy. And he said, you're standing in it. This was Lady Cliff Academy. West Point bought it a few years ago as part of their thing. And then this woman recognized me there, and she came up to me and she was so happy to see me. She gave me this big hug, was just so excited. And I was in that place, in that moment, and I felt like I was somehow connecting with my mother in that moment. There are those types of things that happen every once in a while, but then for me, I can just, like, sort of sit with these images. I have, like, a screensaver on my computer of me and my mom when I was, like, nine years old. And those are these kind of touchstones where I feel, okay, kind of just like going there and opening up and letting down the shields and just trying to be with them, you know?

[A]

I stopped doing this podcast after the first season was just kind of overwhelming. And I had solicited voicemails from listeners, and we got calls from people about their grief. And I listened over the course of about four months. And I still wasn't gonna do any more podcasts, but it made me go back down the basement and start going through these boxes again, which I stopped. And the first box I opened up was a box of my dad's papers. He was a writer. And I randomly picked this box and I opened up a file, first file. And it was an essay called the Importance of Grieving that he had written. And it was about the importance of children grieving and what happens to kids who don't grieve and how they go through their life with a certain melancholy they can never quite put their finger on. And I realized that's exactly what I had done. I had shut down as a kid, and my entire life was spent keeping the grief buried. And it made me realize I need to actually.

Grieve. I need to actually feel, allow myself to feel. And that's what I've been doing the last, like, two years. And it's been life changing. It's been extraordinary, but very difficult.

[C]

That feels like, literally like him kind of reaching.

[A]

Yeah. I mean, it's. Again, it's one of those moments, like.

[C]

But that's like. I mean, that's almost undeniable.

[A]

Yeah.

[C]

Yeah. How do you do that in terms of letting yourself feel stuff?

[A]

Well, doing this podcast, talking to people, just learning from other people how to grieve. I mean, I literally am trying to learn how to grieve.

[C]

Love to.

[A]

It's been incredible. I mean, Stephen Colbert, can you tell me what you learned? Stephen Colbert introduced me to the idea of grief as a gift and learning to love the thing you most wish had never happened. There's a guy, Francis Weller, who's talked about, you can develop a companionship with grief. And this notion that others have taught me that you can still have a relationship with somebody. And my relationship with my dad has changed. I know my dad better now than I ever did before. I've read his letters. And you know your dad better now than you did when he was alive because you've read everything there is.

[C]

I definitely agree with that. I feel like the people who are really close to you and that have made an impact and are a part of you. Those relationships go on and continue. I know because how much I think about them or the conversations I have in my head with them. But. But overall, I think the relationship with my parents has become. I'm much more connected and interested. And now, besides being this age and being able to look at them through the eyes of having gone through a lot of experiences and having a lot more empathy for them, I just kind of also can really appreciate them. And maybe, like five times a week, people will come up to me about my parents saying, like, this happened to me. Your dad did this for me. Your mom said this to me. Your mom told me to fuck off this time or whatever. Cause she had a. You know, I always have, like, a story of my mom saying to somebody, oh, get the fuck out of here. Cause she loved to, you know, sort of test people that way. I feel. She feels so alive. She's such an interesting, smart. I have such an appreciation for her and my dad. I do feel like it's opened up a conversation with people, like the way, you know, you talking to people. But I think it's also.

The understanding a little bit more what it is to be a person and that I just feel. I feel better. I feel a little better about all of it, you know, like. Because it's out in the open.

[A]

Well, even talking about, you know, your mom's drinking.

[C]

Exactly. Once I saw that, it actually was, like, kind of opening up these conversations with people about their own experiences, which you were saying, which, by the way.

[A]

Are conversations that are sorely needed and people are desperate to have. But it's just not something we really allow in society. It's just not something we hold space.

[C]

For to use it. Especially in television, too. That's why the other part I was really fascinated with making the movie was the archival 70s interviews. Gene Shallet, all those. Mike Douglas, all those people, like the stars.

[A]

David Susskind.

[C]

David Susskind. These conversations that people would have on TV in that era were much more real.

[A]

Yeah.

[C]

And that is the stuff that nobody talks about. Like, you can't talk about death, really, on a TV talk. I love Jimmy Fallon, but, like, I'm not gonna talk about death on the Tonight Show. And you go out and you wanna have fun and be funny, but, like, the minute something comes up in your head where you go like, oh, that's something about disease or death or something, it's like, oh, I can't talk about that. Well, it's funny.

[A]

I do New Year's Eve with Andy Cohen.

[C]

Yes, you do.

[A]

And he's always like, okay. And he's very much programming the. And so he'll be like, okay, we'll do your grief. Two minutes. You get two minutes on grief. Do your grief thing.

[C]

Andy's relationship with grief, that's what I want.

[A]

He's the happiest person I've ever met. I mean, he's. Thankfully, both his parents are there, and they're amazing. But it's interesting to me because on New Year's Eve, I will talk about grief because as a child, I was watching the Dick Clark ball drop. My dad was in a Hospital in 1978. I was 10 years old, and he died five days later. And I remember watching the ball drop and just knowing something terrible was gonna happen in this new year and me mentioning it in the minute or two that Andy allows me to on New Year's Eve. I cannot tell you the people who have reached out to me saying, you know what? I was watching the ball drop and really sad, and it's such a difficult night. And it meant so much that you said this thing about, you know, I see. See you out there if you're missing somebody. And I'm sure you will find that as people see the film, just people coming up to you and talking about your parents to you. And it opens up a conversation, which is actually the most meaningful conversations I have. And I get to have them all day long because people literally stop me everywhere I go to talk about people they've lost. And it's beautiful.

[C]

It's so valuable.

[A]

Do you have any regrets? Because there's a recording that your dad made of he and your mom talking, and your mom just gotten off the phone with you and she's sad and she's like, oh, he was clipped. And your dad was like, what? He didn't want to talk to you. Which made me feel bad about not spending more time with my mom.

[C]

Yeah, that was actually one of the most uncomfortable things for me to hear when I found that, because that was being like, you're in the bathroom in high school and hear someone talking about you. You know what I mean? But yet they're talking about their son.

[A]

And it's your parents.

[C]

I know. And they're talking about, like, their son doesn't really want to hang out with them. But the thing is, I don't feel sad for them. I feel bad that I was not able to really appreciate, you know, I feel bad that I was so not self aware or so wrapped up in my own stuff at the time. Now.

With a 20 year old and a 20, almost 24 year old. I'm lucky when I get a call from them during the week that they actually even want to talk or hang out because they're doing their own thing. So it is a natural thing that happens. But I really kind of go more to like, oh God, I was so wrapped up in the work at that point. It was probably like what my son said, I would get in my head and disappear a little bit.

[A]

You had advanced prostate cancer that you found out about and had to have surgery for. Did that make you think about your mortality?

[C]

Oh my God, yeah. When you get a diagnosis like that, everything stops. You know, all your plans, all your thoughts, my job, my. It's like all of it's like, wait a minute, this is something that could change everything. It was scary. Definitely scary.

Nothing like the feeling of relief when you get the call from the doctor, hey, the blood test came back, your PSA is zero. You're cancer free and you want to hold on to that feeling. For me, I think it's 11 years now.

That feeling of gratitude. And I still do have that. But of course it goes up and down. You get wrapped up in things. But what I find even more kind of disturbing though is I hear about people my age. Bill Burr has a funny routine about people just dropping dead. It's age, guys, 50s, 60s are just drop dead. That's very disconcerting because again, it's like we have all these plans and ideas and things we're doing, but it all could just be like, no, it's over. And honestly, if it was over tomorrow, it wouldn't be like, oh yeah, he died kind of young but you know, he had a life.

Right?

[A]

Ben Stiller, thank you so much.

[C]

Thanks, man.

[A]

Ben Stiller's film about his parents, Stiller and Mira. Nothing is Lost is out now. You can watch it on Apple TV next week. My conversation with actor Kelsey Grammer, whose 18 year old sister Karen was murdered when Kelsey was 20. We talk about her loss and others he's experienced and the role that grief has played in his life.

[C]

There was always a note of tragedy in my life.

[A]

Karen's murder was so horrible and so.

[C]

Overwhelming that I couldn't do anything but keep it with me. It stayed beside me for a long time and even though I would still have moments when I would like live very well and happily, it would always come sneaking back in. And I think that's okay.

[A]

That's next week on All There Is.

[C]

It.

[A]

Now streaming on CNN.

[C]

Candid conversations between Hollywood's hottest actors. New episodes of Variety's acclaimed series Actors on Actors premiere exclusively on CNN. Go to CNN.com watch to subscribe or.

[A]

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